Playboy Magazine founder Hugh Hefner died this week at 91, an icon of the American sex revolution and having endured a painful, emotionally-taxing federal drug probe at the height of his fame and popularity in the 1970s. Hefner and his Playboy empire were the high-priority targets of a high-profile, yet ultimately unsuccessful multi-year narcotics probe that concluded in 1975 with the suicide of Hefner’s 34-year old female personal assistant, executive secretary and close friend, Bobbie Arnstein on the heels of a cocaine-trafficking conviction herself.

The U.S. Department of Justice shut down the investigation shortly after Arnstein’s death citing lack of evidence. It certainly wasn’t due to a lack of trying.

The feds aggressively hounded Hefner for close to four years, intent on proving that he was benefiting from a massive drug distribution conspiracy, using his two mansions (one in his hometown of Chicago and the other in L.A) and a series of popular nightclubs and resorts he had stationed around the world for laundering the illegal proceeds and ports of sale. Despite its exhaustive efforts, the government couldn’t directly link Hefner to any illegal activity.

“Hef” started Playboy, the first mainstream nude-pictorial, in 1953 and turned it into a staple of western-world pop culture and multi-million dollar kingdom of cool at a time where conservative values dominated the mainstream.

Like Hefner himself, Roberta “Bobbie” Arnstein came from a Jewish family in Chicago. She began working at Playboy headquarters in downtown Chicago right out of high school. After briefly dating Hefner, she quickly transitioned to his “social secretary” and moved into an apartment at the first Playboy mansion, located on State Street in Chicago’s exclusive Gold Coast section.

Arnstein oversaw the risqué activities at the mansion whenever Hefner was away and ran his day-to-day meeting and appointment schedule in the years before he moved out to California full time. When she reached her 30s, Arnstein began dating younger men and fell into a romance with a 22-year old drug dealer named Ron Scharf. Due to his relationship with Arnstein, Scharf became the Chicago Playboy Mansion’s main narcotics supplier.

Once holding a stringent anti-drug stance, Hefner warmed to the counter-culture once he discovered that marijuana enhanced his sex life. Reports of abundant cocaine use at Playboy parties in Chicago and the then newly-opened and now lone-standing L.A. mansion were rampant, as the soirees began attracting an increasingly jet-set, celebrity crowd and getting constantly written up in media gossip columns.

At some point in early 1971, the government became convinced that Hefner was allowing a wide range of drug-dealing business to transpire at his mansion estates, clubs and resorts and suspected he was pocketing cash in the form of kickbacks on the transactions. The FBI and DEA focused in on the relationship between Bobbie Arnstein and Ron Scharf, a young man they had already heard from informants was in the process of constructing a vast network of cocaine, marijuana and pills customers spread across the affluent north shore suburbs of Chicago

The cocaine Scharf was receiving from his connection in Florida came straight from Bolivia and it was the drug-dealing operation in the Sunshine State that drew the feds attention to Sharf in the first place. Tapping Sharf’s phone and having his Florida contacts heavily monitored, investigators hoped that Scharf would lead them to Arnstein and Arnstein, in turn, to Hefner.

Bobbie Arnstein

Those testifying in front of a grand jury related to the Playboy drug investigation told of wild parties being hosted by Hefner where he passed around bowls of cocaine for his guests to partake in. Several Hollywood movie and television stars were called in front of the grand jury, one of whom, after being granted immunity, admitted to helping supply mansion parties with cocaine. More than one Playboy Club member testified that they were provided controlled substances by club employees during a number of their visits.

On September 15, 1971, federal agents followed Scharf to Florida, where he negotiated a large cocaine deal (6 pounds) with George Matthews, his supplier and a wholesale drug trafficker from Coral Gables. Matthews got his drugs from a source in Jamaica who was tied into the Bolivian coke market. The next week, on September 23, they tracked Scharf and Arnstein on a flight from Chicago to Florida to meet Matthews and secure a part of the deal – a half-pound of blow –, which Arnstein carried back on the plane to Illinois in her purse.

The bug on Scharf’s phone line intercepted conversations with Arnstein requesting some “dynamite coke” for mansion parties and a hand-to-hand sale by Scharf to a wired-up FBI informant in November 1971 proved the final straw. A federal drug indictment landed in February 1972, nailing Scharf and Matthews, but sparing Arnstein for the time being. The government tried to leverage the potential charges over her head as a means of getting her to flip on Hefner, pulling her into dozens of interrogation sessions with the FBI and DEA offices in Chicago. U.S. Attorney Bill Thompson even informed her of a murder contract placed on her head, implying that it came from Hefner or those acting on his behalf.

Still, she steadfastly refused to give in nor give up her friend, former lover and boss. Arnstein’s days of avoiding charges were waning. Finally, on the afternoon of March 23, 1974, she was arrested by DEA agents as she walked out of Chicago’s Playboy Mansion to attend a lunch date. Her name was added to the original indictment and by the end of the year, she would go on trial and be convicted. The conviction was based primarily on the testimony of George Matthews, who had cut a deal and fingered her and Scharf in the September 1971 coke transaction witnessed by federal agents.

Scharf was sentenced to six years in prison, while Arnstein was slammed with a 15-year term, to many an obvious extra-harsh punishment for denying the government its bloodlust in its quest to topple Hefner and what it perceived he represented. Distraught by the prospect of prison, Arnstein committed suicide on January 12, 1975, checking into the Maryland Hotel some 10 blocks south of the Chicago Playboy Mansion and overdosing on sleeping pills. Less than a year later, in December 1975, the U.S. Department of Justice discontinued the Playboy drug probe, quietly issuing a press release stating there wasn’t enough credible evidence to proceed with the investigation. Hefner sold the Windy City mansion soon thereafter and moved full-time to the west coast.